JP2007508309A - Coated metal pyrithione particles for treating microorganisms - Google Patents
Coated metal pyrithione particles for treating microorganisms Download PDFInfo
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- JP2007508309A JP2007508309A JP2006534294A JP2006534294A JP2007508309A JP 2007508309 A JP2007508309 A JP 2007508309A JP 2006534294 A JP2006534294 A JP 2006534294A JP 2006534294 A JP2006534294 A JP 2006534294A JP 2007508309 A JP2007508309 A JP 2007508309A
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- particles
- pyrithione
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- 239000002245 particle Substances 0.000 title claims abstract description 102
- FGVVTMRZYROCTH-UHFFFAOYSA-N pyridine-2-thiol N-oxide Chemical compound [O-][N+]1=CC=CC=C1S FGVVTMRZYROCTH-UHFFFAOYSA-N 0.000 title claims abstract description 53
- 229960002026 pyrithione Drugs 0.000 title claims abstract description 28
- 229910052751 metal Inorganic materials 0.000 title claims description 8
- 239000002184 metal Substances 0.000 title claims description 8
- 244000005700 microbiome Species 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 61
- 239000002453 shampoo Substances 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 17
- 230000000699 topical effect Effects 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 239000011248 coating agent Substances 0.000 claims description 57
- 238000000576 coating method Methods 0.000 claims description 57
- 229940043810 zinc pyrithione Drugs 0.000 claims description 38
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000006185 dispersion Substances 0.000 claims description 31
- 239000007787 solid Substances 0.000 claims description 26
- 235000019482 Palm oil Nutrition 0.000 claims description 24
- 239000002540 palm oil Substances 0.000 claims description 24
- 239000000463 material Substances 0.000 claims description 21
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 17
- 239000000194 fatty acid Substances 0.000 claims description 17
- 229930195729 fatty acid Natural products 0.000 claims description 17
- 239000003960 organic solvent Substances 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- 230000000052 comparative effect Effects 0.000 claims description 11
- -1 fatty acid esters Chemical class 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 230000000845 anti-microbial effect Effects 0.000 claims description 10
- 150000004665 fatty acids Chemical class 0.000 claims description 10
- 238000004166 bioassay Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000003921 oil Substances 0.000 claims description 7
- 235000019198 oils Nutrition 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 230000000844 anti-bacterial effect Effects 0.000 claims description 6
- 229910052725 zinc Inorganic materials 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- 239000012141 concentrate Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003240 coconut oil Substances 0.000 claims description 4
- 235000019864 coconut oil Nutrition 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 235000012343 cottonseed oil Nutrition 0.000 claims description 3
- 239000002385 cottonseed oil Substances 0.000 claims description 3
- 235000021323 fish oil Nutrition 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 239000002600 sunflower oil Substances 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004166 Lanolin Substances 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000010775 animal oil Substances 0.000 claims description 2
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 235000019388 lanolin Nutrition 0.000 claims description 2
- 229940039717 lanolin Drugs 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 150000003626 triacylglycerols Chemical class 0.000 claims description 2
- 150000003754 zirconium Chemical class 0.000 claims description 2
- 235000014121 butter Nutrition 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003925 fat Substances 0.000 claims 1
- 235000019197 fats Nutrition 0.000 claims 1
- 125000005456 glyceride group Chemical group 0.000 claims 1
- 230000000843 anti-fungal effect Effects 0.000 abstract description 8
- 208000001840 Dandruff Diseases 0.000 abstract description 7
- 238000012360 testing method Methods 0.000 description 9
- 229940121375 antifungal agent Drugs 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- 241000555688 Malassezia furfur Species 0.000 description 6
- 210000003491 skin Anatomy 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- 150000002632 lipids Chemical class 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 210000004761 scalp Anatomy 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 4
- 239000004205 dimethyl polysiloxane Substances 0.000 description 4
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 4
- 239000010685 fatty oil Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229920001651 Cyanoacrylate Polymers 0.000 description 3
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 description 3
- 235000013871 bee wax Nutrition 0.000 description 3
- 239000012166 beeswax Substances 0.000 description 3
- 229940008099 dimethicone Drugs 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 125000005233 alkylalcohol group Chemical group 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000011496 digital image analysis Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000001878 scanning electron micrograph Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- 239000004604 Blowing Agent Substances 0.000 description 1
- YDNKGFDKKRUKPY-JHOUSYSJSA-N C16 ceramide Natural products CCCCCCCCCCCCCCCC(=O)N[C@@H](CO)[C@H](O)C=CCCCCCCCCCCCCC YDNKGFDKKRUKPY-JHOUSYSJSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000001135 Friedman test Methods 0.000 description 1
- 241000555676 Malassezia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CRJGESKKUOMBCT-VQTJNVASSA-N N-acetylsphinganine Chemical compound CCCCCCCCCCCCCCC[C@@H](O)[C@H](CO)NC(C)=O CRJGESKKUOMBCT-VQTJNVASSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 235000019498 Walnut oil Nutrition 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229920013822 aminosilicone Polymers 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229940106189 ceramide Drugs 0.000 description 1
- ZVEQCJWYRWKARO-UHFFFAOYSA-N ceramide Natural products CCCCCCCCCCCCCCC(O)C(=O)NC(CO)C(O)C=CCCC=C(C)CCCCCCCCC ZVEQCJWYRWKARO-UHFFFAOYSA-N 0.000 description 1
- 239000011247 coating layer Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- QHNCWVQDOPICKC-UHFFFAOYSA-N copper;1-hydroxypyridine-2-thione Chemical compound [Cu].ON1C=CC=CC1=S.ON1C=CC=CC1=S QHNCWVQDOPICKC-UHFFFAOYSA-N 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- WSDISUOETYTPRL-UHFFFAOYSA-N dmdm hydantoin Chemical compound CC1(C)N(CO)C(=O)N(CO)C1=O WSDISUOETYTPRL-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 239000008266 hair spray Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000008173 hydrogenated soybean oil Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- VVGIYYKRAMHVLU-UHFFFAOYSA-N newbouldiamide Natural products CCCCCCCCCCCCCCCCCCCC(O)C(O)C(O)C(CO)NC(=O)CCCCCCCCCCCCCCCCC VVGIYYKRAMHVLU-UHFFFAOYSA-N 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002374 sebum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/006—Antidandruff preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/555—Heterocyclic compounds containing heavy metals, e.g. hemin, hematin, melarsoprol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Birds (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cosmetics (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Detergent Compositions (AREA)
- Medicinal Preparation (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Abstract
Description
本発明は、被覆されたピリチオン塩粒子で、その被覆によりピリチオン部分の効能が改良され、それによりその組成物により与えられる抗菌効能の持続時間を増大した被覆ピリチオン塩粒子に関する。前記組成物は、人のケアー組成物、特にシャンプー中に配合すると、抗菌、特に抗真菌効能を与えるのに有用である。 The present invention relates to coated pyrithione salt particles, wherein the coating improves the efficacy of the pyrithione moiety, thereby increasing the duration of the antimicrobial efficacy provided by the composition. The composition is useful for providing antibacterial, especially antifungal efficacy, when formulated in human care compositions, particularly shampoos.
シャンプーでは、被覆の親油性が、頭皮、特に、ふけを生ずることが知られている親油性酵母のような親油性微生物を含む頭皮の部位への標的送達を達成し易くする。本発明の被覆粒子を含むシャンプーは、被覆されていないピリチオン塩粒子を含むシャンプーと比較して、増大した抗真菌効能を示す。 In shampoos, the lipophilicity of the coating makes it easier to achieve targeted delivery to the scalp, particularly to sites of the scalp that contain lipophilic microorganisms such as lipophilic yeasts known to cause dandruff. Shampoos comprising the coated particles of the present invention exhibit increased antifungal efficacy compared to shampoos comprising uncoated pyrithione salt particles.
亜鉛及び銅ピリチオンのような金属ピリチオンは、効果的な抗菌剤としてよく知られている。亜鉛ピリチオンは、シャンプーのふけ防止及び抗真菌成分として活性であることがよく知られており、広く用いられている。 Metal pyrithiones such as zinc and copper pyrithione are well known as effective antimicrobial agents. Zinc pyrithione is well known to be active as a shampoo anti-dandruff and antifungal component and is widely used.
PTC特許出願WO 03/007900には、ふけを処理するため皮膚及び頭皮中の脂質のレベルを増大するように、亜鉛ピリチオンと共にセラミドのような親油性剤を使用することが記載されている。しかし、シャンプー配合物中に脂質とピリチオン塩との混合物を使用することは、頭皮の或る場所に脂質を優先的到達させ、別の場所にピリチオン塩が送達されたりすることがある欠点を有する。 PTC patent application WO 03/007900 describes the use of lipophilic agents such as ceramide with zinc pyrithione to increase the level of lipids in the skin and scalp to treat dandruff. However, the use of a mixture of lipid and pyrithione salt in a shampoo formulation has the disadvantage of preferentially reaching the lipid to one location on the scalp and delivering the pyrithione salt to another location. .
本発明は、ピリチオン粒子の上に脂質被覆を用いて、単一のパッケージとして脂質及びピリチオンを標的送達し易くすることにより、前記欠点に対処するものである。 The present invention addresses the above disadvantages by using a lipid coating on the pyrithione particles to facilitate targeted delivery of the lipid and pyrithione as a single package.
一つの態様として、本発明は、部分的又は完全に親油性剤で被覆された、一価及び多価ピリチオン塩、及びそれらの組合せからなる群から選択されたピリチオン塩の被覆された粒子を含む組成物に関する。この組成物は、シャンプーに増大した抗真菌及びふけ防止効能を与える。 In one embodiment, the present invention comprises coated particles of pyrithione salts selected from the group consisting of monovalent and polyvalent pyrithione salts, and combinations thereof, partially or fully coated with a lipophilic agent. Relates to the composition. This composition provides shampoos with increased antifungal and antidandruff efficacy.
別の態様として、本発明は、局所的なキャリヤー、及び部分的又は完全に親油性剤で被覆された、一価及び多価ピリチオン塩、及びそれらの組合せからなる群から選択されたピリチオン塩の被覆された粒子を含む人のケアー組成物、好ましくはシャンプーに関する。 In another aspect, the invention provides a pyrithione salt selected from the group consisting of topical carriers and mono- and polyvalent pyrithione salts, and combinations thereof, partially or fully coated with a lipophilic agent. It relates to a human care composition comprising coated particles, preferably a shampoo.
更に別の態様として、本発明は、固体亜鉛ピリチオン粒子で、その外側表面上に固体パーム油被覆を有する固体亜鉛ピリチオン粒子の水性分散物を製造する方法において、
(a) 固体亜鉛ピリチオン粒子の水性分散物を、約50℃〜約80℃の上昇させた温度へ加熱し、高温水性分散物を与える工程、
(b) 固体パーム油を、約50℃〜約80℃の上昇させた温度へ加熱し、液体パーム油を与え、そして
(c) 前記液体パーム油と、前記高温水性分散物とを混合して混合物を与え、前記混合物を冷却して前記固体パーム油の被覆を有する固体亜鉛ピリチオン粒子の水性分散物を与える工程、
を含む製造方法に関する。得られた分散物は、その分散物の全重量に基づき、約40%〜約50%の量で、適切に被覆された亜鉛ピリチオン粒子を含む。
In yet another aspect, the present invention provides a method for producing an aqueous dispersion of solid zinc pyrithione particles having solid palm oil coating on its outer surface with solid zinc pyrithione particles.
(A) heating an aqueous dispersion of solid zinc pyrithione particles to an elevated temperature of about 50 ° C. to about 80 ° C. to provide a high temperature aqueous dispersion;
(B) heating solid palm oil to an elevated temperature of about 50 ° C. to about 80 ° C. to provide liquid palm oil; and (c) mixing the liquid palm oil with the high temperature aqueous dispersion. Providing a mixture and cooling the mixture to provide an aqueous dispersion of solid zinc pyrithione particles having the solid palm oil coating;
It relates to the manufacturing method containing. The resulting dispersion contains suitably coated zinc pyrithione particles in an amount of about 40% to about 50%, based on the total weight of the dispersion.
更に別の態様として、本発明は、分散物の全重量に基づき、水、及び約25重量%〜約50重量%の固体ピリチオン塩粒子を含む水性抗菌分散濃厚物に関する。固体ピリチオン塩粒子は、その外側表面に親油性被覆を有する被覆された粒子である。それら被覆粒子は、比較コルネオファンジメトリー(corneofungimetry)生物検定試験で、前記ピリチオン塩の被覆されていない粒子の分散物の前記生物検定試験での抗菌効能と比較して、少なくとも25%の抗菌効能改良を示す。別の態様は、人のケアー組成物で、その人のケアー組成物の全重量に基づき、局所的キャリヤー及び約0.5%〜約5%の前記濃厚物を含む人のケアー組成物に関する。人のケアー組成物は、比較コルネオファンジメトリー生物検定試験で、前記ピリチオン塩の被覆されていない粒子の分散物を同じ量で含む人のケアー組成物の前記生物検定試験での抗菌効能と比較して、少なくとも15%の抗菌効能改良を示す。 In yet another aspect, the present invention relates to an aqueous antimicrobial dispersion concentrate comprising water and about 25 wt% to about 50 wt% solid pyrithione salt particles, based on the total weight of the dispersion. Solid pyrithione salt particles are coated particles having a lipophilic coating on their outer surface. The coated particles have at least 25% antimicrobial efficacy in a comparative corneofungimetry bioassay test compared to the antimicrobial efficacy in the bioassay test of the dispersion of the uncoated particles of pyrithione salt. Indicates an improvement. Another aspect relates to a human care composition comprising a topical carrier and from about 0.5% to about 5% of the concentrate, based on the total weight of the person's care composition. The human care composition is compared with the antimicrobial efficacy of the human care composition containing the same amount of the uncoated particles of pyrithione salt in the comparative corneophanemetry bioassay test. An antibacterial efficacy improvement of at least 15%.
これら及び他の態様は、本発明についての次の詳細な記述を読むことにより明らかになるであろう。 These and other aspects will become apparent upon reading the following detailed description of the invention.
本発明の詳細な記述
今回、親油性脂肪油被覆を含む被覆されたピリチオン粒子が、頭皮の希望の親油性部位にピリチオンを送達するのに効果的な伝達手段を与えることが思いがけなく発見された。これらの部位では、ふけを生ずることが知られている親油性Malassezia sp イーストのような親油性微生物が見出される傾向がある。これらの部位を標的とする送達は、これらの被覆ピリチオン粒子を含有するシャンプーの抗真菌及びふけ防止効能を、被覆されていないピリチオン粒子を含むシャンプーと比較して増大する。
Detailed Description of the Invention It has now been unexpectedly discovered that coated pyrithione particles comprising a lipophilic fatty oil coating provide an effective vehicle for delivering pyrithione to the desired lipophilic site of the scalp. At these sites there is a tendency to find lipophilic microorganisms such as lipophilic Malassezia sp yeast that are known to cause dandruff. Delivery targeted to these sites increases the antifungal and anti-dandruff efficacy of shampoos containing these coated pyrithione particles compared to shampoos containing uncoated pyrithione particles.
本発明で用いられるピリチオン粒子は、亜鉛、銅、銀、ジルコニウムの塩、及びそれらの組合せからなる群から選択されるのが好ましい。一層好ましいピリチオン塩は、亜鉛及び銅の塩から選択され、最も好ましくは亜鉛塩である。亜鉛塩は、粒状分散物、スラリー、又は粉末の形で適切に用いられる。亜鉛ピリチオンは、例えば、板状子、棒状、針状、ブロック状、球状、及び無定形、規則的又は不規則な形をした粒子のような結晶形態を含むどのような粒子形態で用いてもよい。亜鉛ピリチオン粒子の平均粒子直径(最大寸法)が、例えばホリバ(Horiba)LA−910レーザー散乱粒径分布分析器を用いて決定して、典型的には、約0.1〜約50μmであり、好ましくは約0.1μm〜約10μm、一層好ましくは約0.1μm〜約5μmである。 The pyrithione particles used in the present invention are preferably selected from the group consisting of zinc, copper, silver, zirconium salts, and combinations thereof. More preferred pyrithione salts are selected from zinc and copper salts, most preferably zinc salts. Zinc salts are suitably used in the form of granular dispersions, slurries or powders. Zinc pyrithione may be used in any particle form, including, for example, crystalline forms such as platelets, rods, needles, blocks, spheres, and amorphous, regular or irregular shaped particles. . The average particle diameter (maximum dimension) of the zinc pyrithione particles is typically about 0.1 to about 50 μm, as determined using, for example, a Horiba LA-910 laser scattering particle size distribution analyzer, The thickness is preferably about 0.1 μm to about 10 μm, more preferably about 0.1 μm to about 5 μm.
本発明の被覆粒子上の親油性被覆は、室温で固体又は液体である合成又は天然の脂肪油を含む。従って、ここで用いられる用語「親油性剤」とは、油及びワックスの両方を包含するものとする。脂肪油は、約150〜約1500の範囲内の数平均分子量、及び8〜22の範囲内の炭素数を有する脂肪酸又は脂肪酸エステル、又はそれらの混合物を含む。脂肪酸エステルは、モノ−、ジ−、又はトリ−グリセリド、又はそれらの混合物を含むことができる。好ましい被覆材料は、パーム油である。 The lipophilic coating on the coated particles of the present invention comprises a synthetic or natural fatty oil that is solid or liquid at room temperature. Thus, as used herein, the term “lipophilic agent” is intended to encompass both oils and waxes. The fatty oil comprises a fatty acid or fatty acid ester having a number average molecular weight in the range of about 150 to about 1500 and a carbon number in the range of 8 to 22, or mixtures thereof. Fatty acid esters can include mono-, di-, or tri-glycerides, or mixtures thereof. A preferred coating material is palm oil.
親油性被覆成分が占める割合は、被覆ピリチオン粒子の全重量に基づき、好ましくは0.01重量%より大きく、好ましくは1重量%より大きく、一層好ましくは3重量%より大きい。典型的には、被覆粒子中の親油性剤含有量は、約3〜15%の範囲にある。1重量%の亜鉛ピリチオンを含有するシャンプーでは、親油性被覆薬剤の量は、シャンプーの重量に基づき、一般に約0.001重量%〜約0.15重量%、好ましくは約0.01重量%〜約0.15重量%、一層好ましくは約0.03重量%〜約0.15重量%である。 The proportion occupied by the lipophilic coating component is preferably greater than 0.01% by weight, preferably greater than 1% by weight, more preferably greater than 3% by weight, based on the total weight of the coated pyrithione particles. Typically, the lipophilic agent content in the coated particles is in the range of about 3-15%. For shampoos containing 1% by weight zinc pyrithione, the amount of lipophilic coating agent is generally from about 0.001% to about 0.15% by weight, preferably from about 0.01% to about 0.1%, based on the weight of the shampoo. About 0.15 wt%, more preferably about 0.03 wt% to about 0.15 wt%.
適当な脂肪酸及び脂肪酸エステルには、炭化水素油、ワックス、ジ−、及びトリ−グリセリド油が含まれ、例えば、ワセリン、鉱油ワックス、水素化及び非水素化ポリアルケン、水素化油、パラフィン、合成パラフィン、ポリエチレン及びポリブテンパーム油、ひまし油、大豆油、誘導体化大豆油、例えば、ひまわり油、綿実油、コーン油、くるみ油、落花生油、胡麻油、植物油、植物油誘導体、ココナッツ油、ココナッツ油誘導体が含まれる。 Suitable fatty acids and fatty acid esters include hydrocarbon oils, waxes, di- and triglyceride oils, such as petrolatum, mineral oil wax, hydrogenated and non-hydrogenated polyalkenes, hydrogenated oils, paraffins, synthetic paraffins. Polyethylene and polybutene palm oil, castor oil, soybean oil, derivatized soybean oil, such as sunflower oil, cottonseed oil, corn oil, walnut oil, peanut oil, sesame oil, vegetable oil, vegetable oil derivative, coconut oil, coconut oil derivative.
脂肪酸/脂肪酸エステルは、天然産又はそれらの誘導体にすることができる。被覆の炭素鎖の長さは、一般にC8〜C22であり、それらの混合物が含まれる。脂肪酸は、飽和及び不飽和、線状及び分岐鎖脂肪酸にすることができる。それらは、脂肪酸及びそれらからの誘導体の化学的及び物理的性質に基づき選択される。 The fatty acid / fatty acid ester can be naturally occurring or derivatives thereof. The carbon chain length of the coating is generally C8-C22 and includes mixtures thereof. The fatty acids can be saturated and unsaturated, linear and branched chain fatty acids. They are selected based on the chemical and physical properties of the fatty acids and their derivatives.
脂肪酸及びそれらの誘導体の適当な天然及び合成源には、動物及び植物起源のもの、例えば、ラノリン油、魚油、動物油、ココナッツ油、パーム油、バター脂肪、大豆油、ひまわり油、綿実油、コーン油、及びそれらの混合物が含まれる。好ましい脂肪酸源は、パーム油、部分的及び完全に水素化した脂肪油、脂肪酸、例えば、水素化大豆油、パーム油、パームカーネル油、魚油、ポリオール脂肪酸エステルである。 Suitable natural and synthetic sources of fatty acids and their derivatives include those of animal and plant origin, such as lanolin oil, fish oil, animal oil, coconut oil, palm oil, butterfat, soybean oil, sunflower oil, cottonseed oil, corn oil And mixtures thereof. Preferred fatty acid sources are palm oil, partially and fully hydrogenated fatty oils, fatty acids such as hydrogenated soybean oil, palm oil, palm kernel oil, fish oil, polyol fatty acid esters.
一つの別の仕方として、親油性被覆剤は室温で固体であり、上昇させた温度で液体になり、冷却してフィルムを形成する。固体被覆材料は、約40〜100℃で液体になり、次に冷却する間にフィルムを形成することができるのが望ましい。別法として、親油性被覆剤は、適当に溶媒に溶解し、それを乾燥させるとフィルムを形成する。例として被覆剤を有機溶媒、例えば、メタノール及びエタノールのようなアルキルアルコール、アセトン、エーテル、ハロゲン化炭化水素、及び芳香族溶媒の中に適当に溶解し、次にその溶媒を蒸発させる間にフィルムを形成する。 As an alternative, the lipophilic coating is solid at room temperature, becomes liquid at elevated temperatures, and cools to form a film. Desirably, the solid coating material becomes liquid at about 40-100 ° C. and can form a film during subsequent cooling. Alternatively, the lipophilic coating is suitably dissolved in a solvent and dried to form a film. By way of example, the coating is suitably dissolved in an organic solvent, for example an alkyl alcohol such as methanol and ethanol, acetone, ether, halogenated hydrocarbons, and aromatic solvents, and then the film is evaporated while the solvent is evaporated. Form.
本発明で水中での粒子被覆には、被覆材料が液体状態になっているか、又は溶液状態になっている条件下で、被覆材料を存在させたスラリー又は懸濁状態の金属ピリチオン又はピリチオン粒子の多価塩の被覆が含まれる。被覆した粒子の大きさ、形、及び厚さは、スラリー又は懸濁物中の元の粒子の大きさ及び形、温度、及び用いた被覆材料の量に依存する。この方法は、液体状態の(望ましくは約90℃より低い融点温度で)被覆材料を、その被覆材料が液体状態になっている温度でスラリー又は懸濁物中へ適当な速度で撹拌しながら添加し、次に金属ピリチオンスラリーと被覆成分との混合物、又は被覆材料の混合物を冷却するか、又は用いた被覆材料の最も高い融点温度に加熱し、次に冷却するものとして簡単に記述することができる。 In the present invention, for particle coating in water, a slurry of a coating or a suspended metal pyrithione or pyrithione particle under the condition that the coating material is in a liquid state or a solution state. A polyvalent salt coating is included. The size, shape, and thickness of the coated particles depend on the size and shape of the original particles in the slurry or suspension, the temperature, and the amount of coating material used. This method involves adding a coating material in a liquid state (preferably at a melting temperature below about 90 ° C.) to the slurry or suspension at a temperature at which the coating material is in a liquid state with stirring at an appropriate rate. And then briefly described as a mixture of the metal pyrithione slurry and coating component, or a mixture of coating materials, or heated to the highest melting temperature of the coating material used and then cooled. it can.
有機溶媒中での粒子被覆は、金属ピリチオン又はピリチオン粉末の多価塩を、室温以上の温度で有機溶媒に入れた被覆材料(一種又は多種)の溶液へ添加し、次に撹拌しながら溶媒を蒸発させることを含んでいる。被覆された粒子の大きさ、形、及び厚さは、元の粒子の大きさ、金属ピリチオンの形、及び被覆材料の量及び性質に依存する。 Particle coating in an organic solvent involves adding a metal pyrithione or polyvalent salt of pyrithione powder to a solution of the coating material (one or many) in an organic solvent at a temperature above room temperature, and then stirring the solvent while stirring. Includes evaporation. The size, shape, and thickness of the coated particles depend on the original particle size, the shape of the metal pyrithione, and the amount and nature of the coating material.
重合体被覆材料の融点以上の温度でピリチオンを被覆するのに粉末被覆も適切に用いることができる。液体被覆材料は、冷却する間に、粒子上にフィルム又は被覆層を形成する。被覆した量の大きさ、形、及び被覆の厚さは、金属ピリチオン粒子の元の大きさ及び形、及び用いた被覆材料の量及び性質に依存する。この方法は、低い(好ましくは約90℃より低い)融点を有する材料で粒子を被覆するのに特に適している。 A powder coating can also be suitably used to coat pyrithione at temperatures above the melting point of the polymer coating material. The liquid coating material forms a film or coating layer on the particles while cooling. The size, shape, and coating thickness of the amount coated depends on the original size and shape of the metal pyrithione particles and the amount and nature of the coating material used. This method is particularly suitable for coating particles with materials having a low (preferably less than about 90 ° C.) melting point.
本発明の被覆ピリチオン粒子は、局所的キャリヤーを含む人のケアー組成物に用いるのに適している。局所的キャリヤーは、形成される組成物の種類により、慣用的人のケアーキャリヤーの広い範囲から選択するのが適切である。相容性キャリヤーを適切に選択することにより、ヘヤーリンスのような日常の皮膚又は毛髪用製品、ヘヤーローション、ヘヤースプレー、ヘヤートニック、コンディショニング・トリートメント、及びドレッシングのような日常の毛髪手入れ用品等の形態で、本発明の抗菌組成物を調製できるようにすることが考えられている。 The coated pyrithione particles of the present invention are suitable for use in human care compositions containing a topical carrier. The topical carrier is suitably selected from a wide range of conventional human care carriers, depending on the type of composition being formed. By appropriately selecting a compatible carrier, forms of daily skin or hair products such as hair rinses, daily hair care products such as hair lotions, hair sprays, hair tonics, conditioning treatments, and dressings, etc. Thus, it is considered that the antibacterial composition of the present invention can be prepared.
液体ヘヤー組成物中の局所的キャリヤーは、水、一般的有機溶媒、又はそれらの混合物にすることができる。適当な一般的有機溶媒は、エタノール、プロパノール、イソプロパノール、グリセリンのようなC2−C3アルキルアルコールである。脂肪アルコール及びエステルのような他の溶媒も用いることができる。 The topical carrier in the liquid hair composition can be water, a common organic solvent, or a mixture thereof. Suitable common organic solvents are C2-C3 alkyl alcohols such as ethanol, propanol, isopropanol, glycerin. Other solvents such as fatty alcohols and esters can also be used.
本発明の抗菌組成物は、組成物の重量で、約40%〜約92%、好ましくは約50%〜約85%、一層好ましくは約60%〜約80%の水を含む水性系でもよい。 The antimicrobial composition of the present invention may be an aqueous system comprising about 40% to about 92%, preferably about 50% to about 85%, more preferably about 60% to about 80% water by weight of the composition. .
本発明の組成物がふけ防止シャンプーである場合、組成物のpHは、一般に約2〜約10、好ましくは約3〜約9、一層好ましくは約4〜約8、最も好ましくは約5.5〜約7.5の範囲にある。 When the composition of the present invention is an anti-dandruff shampoo, the pH of the composition is generally about 2 to about 10, preferably about 3 to about 9, more preferably about 4 to about 8, and most preferably about 5.5. Is in the range of ~ 7.5.
次の例は、本発明を例示するためであり、その範囲を何ら限定するものではない。全ての被覆粒子は、ESCA、SEM、及び粒径分布分析器により特徴付けられ、被覆粒径分布中の亜鉛ピリチオンの含有量は、標準滴定法を用いて決定された。 The following examples are intended to illustrate the present invention and are not intended to limit its scope in any way. All coated particles were characterized by ESCA, SEM, and particle size distribution analyzer, and the content of zinc pyrithione in the coated particle size distribution was determined using standard titration methods.
例1
約3.4μのメジアン粒径を有する亜鉛ピリチオン粉末(約200g)を、小さな粒化機中へ入れた。パーム油(約24g)を、ホットプレートの上で溶融し、70℃に維持した加熱供給物容器中に入れた。二つの流体ノズルを加熱追跡し、75℃に維持した。粒化機を始動させ、溶融被覆材料を撹拌粉末中へ噴霧した。
Example 1
Zinc pyrithione powder (about 200 g) having a median particle size of about 3.4μ was placed in a small granulator. Palm oil (about 24 g) was melted on a hot plate and placed in a heated feed container maintained at 70 ° C. The two fluid nozzles were heated and maintained at 75 ° C. The granulator was started and the molten coating material was sprayed into the stirred powder.
被覆粒子は次の特徴を持っていた:
亜鉛ピリチオン分析値:85.8%
粒径〔ホリバ(Horriba)LA−910〕:メジアン(D50):7.44μm;比表面積:2分超音波処理後、17647cm2/cm3。
The coated particles had the following characteristics:
Analysis value of zinc pyrithione: 85.8%
Particle size [Horiba (Horriba) LA-910]: median (D 50): 7.44μm; specific surface area: after 2 min sonication, 17647cm 2 / cm 3.
原子濃度のESCA分析及びZn及びS信号の減衰から誘導された被覆厚さは、被覆の存在が35Åであることを示していた。
被覆粒子のSEM像は、粒子が目で見て被覆されており、クラスターの特徴を有することを示していた。
The coating thickness derived from the ESCA analysis of the atomic concentration and the decay of the Zn and S signals showed that the presence of the coating was 35 mm.
The SEM image of the coated particles showed that the particles were visually coated and had cluster characteristics.
比較例A:
〜65℃のD.I.水150ml中に210.0gの48.0%亜鉛ピリチオン(メジアン粒径0.47μm)を入れた撹拌懸濁物に、60〜65℃のステアリルジメチコン4.1gからなる熱い液体油をゆっくり添加した。この温度で10分間500rpmで撹拌した後、分散物を、300rpmの撹拌速度で徐々に室温へ冷却した。
被覆粒子は、次の特徴を持っていた:
亜鉛ピリチオン分析値:32.0%
粒径(ホリバLA−910):メジアン(D50):0.478μm;平均:0.507μm;比表面積:2分超音波処理後、136981cm2/cm3。
Comparative Example A:
D. of ~ 65 ° C. I. To a stirred suspension of 210.0 g of 48.0% zinc pyrithione (median particle size 0.47 μm) in 150 ml of water was slowly added hot liquid oil consisting of 4.1 g of stearyl dimethicone at 60-65 ° C. . After stirring at 500 rpm for 10 minutes at this temperature, the dispersion was gradually cooled to room temperature with a stirring speed of 300 rpm.
The coated particles had the following characteristics:
Analysis value of zinc pyrithione: 32.0%
Particle size (Horiba LA-910): Median (D 50 ): 0.478 μm; Average: 0.507 μm; Specific surface area: 136811 cm 2 / cm 3 after sonication for 2 minutes.
原子濃度のESCA分析及びZn及びS信号の減衰から誘導された被覆厚さは、表1に示したように、被覆の存在が15Åであることを示していた。被覆粒子のSEM像は、粒子が薄く被覆されていることを示していた。亜鉛ピリチオン粒子(0.1〜1μm、ブロック及び板状子の混合物)は、幾らかの散乱した被覆パッチを有し明確な輪郭をもち、粒子の縁は見かけ上軟化していた。微細亜鉛ピリチオン粒子について見られたように、真っすぐ又は角度のある特徴よりもむしろ湾曲した特徴を有するこれらの被覆に関連した特徴は、元の微細粒子の一部であり、ESCAで見られたように丁度薄い被覆である可能性がある。 The coating thickness derived from the ESCA analysis of atomic concentration and the decay of the Zn and S signals indicated that the presence of the coating was 15 mm, as shown in Table 1. The SEM image of the coated particles showed that the particles were thinly coated. Zinc pyrithione particles (0.1-1 μm, a mixture of blocks and platelets) had some scattered coated patches, had a well-defined profile, and the edges of the particles were apparently softened. As seen for the fine zinc pyrithione particles, these coating-related features with curved features rather than straight or angular features are part of the original fine particles, as seen with ESCA May be just a thin coating.
被覆粒子は、Malassezia furfurに対する定性的阻止帯(Zone of Inhibition)(ZOI)試験で活性を示し、被覆は寒天を通って亜鉛ピリチオンが移動するのを阻止しなかったことを実証していた。 The coated particles showed activity in a Qualitative Zone of Inhibition (ZOI) test against Malassezia furfur, demonstrating that the coating did not block the migration of zinc pyrithione through the agar.
比較例B〜D:
例1−(I)部の手順に従い、48.0%の亜鉛ピリチオン(メジアン粒径0.47μm)の懸濁物中に入れた亜鉛ピリチオン粒子を、アミノ官能性ポリジメチルシロキサン〔アモジメチコン(Amodimethicon)、ダウ・コーニング2−8566アミノ流体、例B〕、レシチン〔セントロミクス(Centromix)LP250、例C〕、及びビス−PEG−12ジメチコン蜜蝋(シリコニル蜜蝋、例D)を用いてその場で被覆した。これらの被覆した亜鉛ピリチオン粒子の特性データーを、表1に記載する。
Comparative Examples B to D:
EXAMPLE 1 Zinc pyrithione particles placed in a suspension of 48.0% zinc pyrithione (median particle size 0.47 μm) according to the procedure of Example 1- (I) were converted to aminofunctional polydimethylsiloxane [Amodimethicon. ), Dow Corning 2-8566 amino fluid, Example B], lecithin [Centromix LP250, Example C], and bis-PEG-12 dimethicone beeswax (Siliconyl beeswax, Example D). did. The characteristic data of these coated zinc pyrithione particles are listed in Table 1.
最初の性能試験では、例1及び比較例の全てが、Malassezia furfurに対する定性的阻止帯(ZOI)試験で被覆粒子抗菌活性を示し、被覆は亜鉛ピリチオンが移動するのを阻止しなかったことを実証していた。 Initial performance tests demonstrated that Example 1 and all of the comparative examples showed coated particle antimicrobial activity in a qualitative zone of inhibition (ZOI) test against Malassezia furfur and the coating did not block the migration of zinc pyrithione. Was.
一層進んだ試験として、「コルネオファンジメトリー」を用いて、例及び比較例に従って調製した粒子を評価した。この試験は、良好な前臨床スクリーニング法である。なぜなら、それは、自然の環境を一層よく代表する基質上でのMalassezia furfur spの増殖を必要とするからである。皮膚層を採取するのにシアノアクリレートを用い、これらの皮膚表面の剥離物をオリーブオイルで処理し、皮脂に類似させる。調製した皮膚試料を、研究中の活性剤で処理し、問題の微生物を接種し、培養した。この研究では、活性剤は、被覆した亜鉛ピリチオン粒子であり、用いた試験有機体はMalassezia furfurであった。処理の相対的効能を、対照と比較して増殖の阻止を探すことにより決定し、このデーターをコンピューターによる画像解析及び生体染色を用いて収集した。それは、被覆亜鉛ピリチオンがMalassezia furfurに対し、被覆していない材料よりも一層効能が高いことを示している。亜鉛ピリチオンの効能を試験するため、1%水性分散物、及びシャンプー配合物中に1%入れた両方を用いた。下の表3に試験結果を示した配合シャンプーは、次の成分を含んでいた:ステパノール(STEPANOL)AM−V陰イオン性表面活性剤、68.3%;ステパン(STEPAN)SAB−2懸濁剤、5%;ニノール(NINOL)40−CO非イオン性発泡剤、2%;被覆亜鉛ピリチオン粒子、ピリチオン含有量に基づき1%;グリダント(GLYDANT)防腐剤、0.3%;100%にするための残余の脱イオン水;全ての重量%はシャンプーの全重量に基づく。 As a further test, the particles prepared according to the examples and comparative examples were evaluated using “Corneophanimetry”. This test is a good preclinical screening method. This is because it requires the growth of Malassezia furfur sp on a substrate that better represents the natural environment. Cyanoacrylate is used to collect the skin layer, and these skin surface exfoliants are treated with olive oil to resemble sebum. The prepared skin samples were treated with the active agent under study, inoculated with the microorganism in question and cultured. In this study, the activator was coated zinc pyrithione particles and the test organism used was Malassezia furfur. The relative efficacy of the treatment was determined by looking for growth inhibition compared to the control, and this data was collected using computer image analysis and vital staining. It shows that coated zinc pyrithione is more effective against Malassezia furfur than uncoated material. To test the efficacy of zinc pyrithione, both a 1% aqueous dispersion and 1% in a shampoo formulation were used. The formulated shampoo, whose test results are shown in Table 3 below, contained the following ingredients: STEPANOL AM-V anionic surfactant, 68.3%; STEPAN SAB-2 suspension NINOL 40-CO nonionic blowing agent, 2%; coated zinc pyrithione particles, 1% based on pyrithione content; GLYDANT preservative, 0.3%; 100% Residual deionized water for; all weight percentages are based on the total weight of the shampoo.
シアノアクリレート接着剤を用いて20人の健康なボランティアから採取した正常な角膜層(stratum corneum)でコルネオファンジメトリー生物検定を行った。試料をオリーブ油中に浸漬し、殺菌環境中に3日間保存した。オリーブ油を含浸させた角膜層試料を、第二段階で亜鉛ピリチオンの1%分散水又は1%の亜鉛ピリチオンを含有するシャンプー中に浸漬した。「コルネオファンジメトリー」試験による更に別の情報が、「臨床及び実験的皮膚病学」(Clinical and Experimental Dermatology)(1989)、第14巻、第425頁〜第428頁に見られるA.ルランギルワ(Rurangirwa)、C.ペイラルド−フランチモント(Peirard-Franchimont)、及びG.E.ピラルド(Pierard)Cによる「シアノアクリレート皮膚表面剥離物上の真菌培養−抗真菌薬剤を評価するための定量的生物検定」(Culture of fungi on cyanoacrylate skin surface strippings-a quantitative bioassay for evaluating antifungal drugs)と題する技術雑誌論文で入手することができる。 Corneophanometry bioassays were performed on normal stratum corneum taken from 20 healthy volunteers using cyanoacrylate glue. Samples were soaked in olive oil and stored in a sterilized environment for 3 days. The corneal layer sample impregnated with olive oil was immersed in a shampoo containing 1% zinc pyrithione dispersion or 1% zinc pyrithione in the second stage. Further information from the “Corneophanometry” test can be found in “Clinical and Experimental Dermatology” (1989), Vol. 14, pp. 425-428. Rurangirwa, C.I. Peirard-Franchimont, and G.M. E. "Pulture of fungi on cyanoacrylate skin surface strippings-a quantitative bioassay for evaluating antifungal drugs" by Pierard C Available in technical journal papers.
Malassezia furfurを、MLMA〔変性リーミング(Modified Leeming)及びノットマン(Notman)寒天〕媒地で培養した。真菌細胞の懸濁物を生理的食塩水(104〜105細胞/ml)に入れて調製した。これらの懸濁物250μl部分を、角膜層試料上に付着させ、27℃で9日間湿潤状態で培養した。試料を、生体染色として天然赤色を用いて染色し、人間の角膜層上に増殖した生きた真菌を同定した。コンピューターによる画像解析(アナリシス・オリンパス)を用いてmm2単位で陽性真菌細胞数を計算した。メジアン及び範囲を決定した。一対の非パラメーター・フリードマン(Friedman)試験を用い、次にダン(Dunn)試験を用いて生成物間比較を行なった。 Malassezia furfur was cultured in MLMA (Modified Leeming and Notman agar) media. A suspension of fungal cells was prepared in physiological saline (10 4 to 10 5 cells / ml). 250 μl portions of these suspensions were deposited on the corneal layer samples and incubated at 27 ° C. for 9 days in a wet state. Samples were stained using natural red as a vital stain to identify live fungi grown on the human corneal layer. The number of positive fungal cells was calculated in mm 2 using computer image analysis (Analysis Olympus). The median and range were determined. A pair of non-parameter Friedman tests were used, followed by a product comparison using the Dunn test.
表2及び3に示したデーターに示されるように、11.7%のパーム油で被覆した試料(例1)は、最もよい抗真菌効能結果(%)を与えることを実証していた。比較として4.0%のステアリルジメチコン(比較例A)は、水分散物及び配合したシャンプーの両方で、被覆していない対照よりも中程度の効能を示したのに対し、7.5%のアミノシリコーンで被覆した試料(比較例B)は、水分散物では幾らか良好な効能の改良を示したが、配合シャンプーでは僅かな改良しか示さなかった。驚いたことに、レシチン(比較例C)及びシリコニル蜜蝋(比較例D)で被覆した試料は、水懸濁物では負の効能改良を示している。 As shown in the data shown in Tables 2 and 3, the sample coated with 11.7% palm oil (Example 1) demonstrated that it gave the best antifungal efficacy results (%). For comparison, 4.0% stearyl dimethicone (Comparative Example A) showed moderate efficacy over both the aqueous dispersion and formulated shampoo over the uncoated control, compared with 7.5% A sample coated with aminosilicone (Comparative Example B) showed some good improvement in efficacy with the aqueous dispersion, but only a slight improvement with the formulated shampoo. Surprisingly, the sample coated with lecithin (Comparative Example C) and siliconyl beeswax (Comparative Example D) shows a negative efficacy improvement in the aqueous suspension.
本発明を、その特別な態様に関連して上に記述してきたが、多くの変化、修正、及び変更を、ここに記載した本発明の概念から離れることなく行うことができることは明らかである。従って、添付の特許請求の範囲の本質及び広い範囲内に入るそのような変化、修正、及び変更は全て包含されるものである。
Although the invention has been described above with reference to specific embodiments thereof, it is apparent that many changes, modifications, and changes can be made without departing from the inventive concepts described herein. Accordingly, it is intended to embrace all such changes, modifications and variations that fall within the essence and broad scope of the appended claims.
Claims (27)
(a) 固体亜鉛ピリチオン粒子の水性分散物を、約50℃〜約80℃の上昇させた温度へ加熱し、高温水性分散物を与える工程、
(b) 固体パーム油を、約50℃〜約80℃の上昇させた温度へ加熱し、液体パーム油を与え、そして
(c) 前記液体パーム油と、前記高温水性分散物とを混合して混合物を与え、前記混合物を冷却して前記固体パーム油の被覆を有する固体亜鉛ピリチオン粒子の水性分散物を与える工程、
を含む、上記製造方法。 In a method of producing an aqueous dispersion of solid zinc pyrithione particles having solid palm oil coating on its outer surface with solid zinc pyrithione particles.
(A) heating an aqueous dispersion of solid zinc pyrithione particles to an elevated temperature of about 50 ° C. to about 80 ° C. to provide a high temperature aqueous dispersion;
(B) heating solid palm oil to an elevated temperature of about 50 ° C. to about 80 ° C. to provide liquid palm oil; and (c) mixing the liquid palm oil with the high temperature aqueous dispersion. Providing a mixture and cooling the mixture to provide an aqueous dispersion of solid zinc pyrithione particles having the solid palm oil coating;
The said manufacturing method containing.
(a) 前記ピリチオン粒子を、有機溶媒中に溶解した被覆材料の溶液と接触させる工程、
(b) 前記ピリチオン粒子を、前記有機溶媒中に入れた前記被覆材料と混合する工程、及び
(c) 前記有機溶媒を蒸発して、前記被覆材料で被覆されたピリチオン粒子を与える工程、
を含むピリチオン粒子被覆方法。 In a method of coating pyrithione particles with a coating material,
(A) contacting the pyrithione particles with a solution of a coating material dissolved in an organic solvent;
(B) mixing the pyrithione particles with the coating material in the organic solvent, and (c) evaporating the organic solvent to give pyrithione particles coated with the coating material;
A pyrithione particle coating method comprising:
27. The method of claim 26, wherein the coating material is palm oil.
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JPH0348604A (en) * | 1989-07-12 | 1991-03-01 | L'oreal Sa | Aqueous gel cosmetic composition containing sphiloid which is non hydrophilic and a lipoid substance in suspension state |
JPH11509220A (en) * | 1995-07-14 | 1999-08-17 | ユニリーバー・ナームローゼ・ベンノートシヤープ | Antimicrobial hair treatment composition |
JPH10245409A (en) * | 1997-03-03 | 1998-09-14 | Amcol Internatl Corp | Oil-and water-absorptive polymer, and its production |
JP2004512349A (en) * | 2000-10-30 | 2004-04-22 | ユニリーバー・ナームローゼ・ベンノートシヤープ | Shear gel composition |
JP2002173410A (en) * | 2000-12-06 | 2002-06-21 | Taiki:Kk | Fine resin particle for cosmetic |
WO2003007900A2 (en) * | 2001-07-18 | 2003-01-30 | Unilever Plc | Skin treatment |
JP2005504812A (en) * | 2001-09-28 | 2005-02-17 | アーチ ケミカルズ,インコーポレイテッド | Dust-free copper pyrithione dispersion |
Cited By (1)
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JP2016523232A (en) * | 2013-06-04 | 2016-08-08 | ビョーメ バイオサイエンシズ ピーブイティー.リミテッド | Coated particles and compositions containing same |
Also Published As
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BRPI0414768B1 (en) | 2015-09-08 |
BRPI0414768A (en) | 2006-11-21 |
ES2369853T3 (en) | 2011-12-07 |
KR101106025B1 (en) | 2012-01-17 |
CN1859899A (en) | 2006-11-08 |
JP4664919B2 (en) | 2011-04-06 |
ATE518524T1 (en) | 2011-08-15 |
EP1675572B1 (en) | 2011-08-03 |
US20050118276A1 (en) | 2005-06-02 |
US8980235B2 (en) | 2015-03-17 |
KR20060109444A (en) | 2006-10-20 |
CN100512876C (en) | 2009-07-15 |
WO2005032489A2 (en) | 2005-04-14 |
EP1675572A4 (en) | 2009-12-23 |
WO2005032489A3 (en) | 2005-11-24 |
NO20061917L (en) | 2006-06-15 |
EP1675572A2 (en) | 2006-07-05 |
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